Ibandronic acid

Chemical compound
  • EU EMA: by INN
  • US DailyMed: Ibandronate_sodium
  • US FDA: Ibandronate_sodium
Pregnancy
category
  • AU: B3
Routes of
administrationBy mouth, intravenousATC code
  • M05BA06 (WHO)
Legal statusLegal status
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic dataBioavailability0.6%Protein binding90.9 to 99.5%
(concentration-dependent)MetabolismNilElimination half-life10 to 60 hoursExcretionKidneyIdentifiers
  • Hydroxy-[1-hydroxy-3-[methyl(pentyl)amino]-1-phosphonopropyl]phosphinate
CAS Number
  • 114084-78-5 checkY
PubChem CID
  • 60852
IUPHAR/BPS
  • 3059
DrugBank
  • DB00710 ☒N
ChemSpider
  • 54839 checkY
UNII
  • UMD7G2653W
KEGG
  • D08056 checkY
  • as salt: D04486 checkY
ChEBI
  • CHEBI:93770
ChEMBL
  • ChEMBL997 checkY
PDB ligand
  • BFQ (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID5048340 Edit this at Wikidata
ECHA InfoCard100.214.537 Edit this at WikidataChemical and physical dataFormulaC9H23NO7P2Molar mass319.231 g·mol−13D model (JSmol)
  • Interactive image
  • O=P(O)(O)C(O)(CCN(CCCCC)C)P(=O)(O)O
  • InChI=1S/C9H23NO7P2/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17) checkY
  • Key:MPBVHIBUJCELCL-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ibandronic acid is a bisphosphonate medication used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer.[1] It may also be used to treat hypercalcemia (elevated blood calcium levels). It is typically formulated as its sodium salt ibandronate sodium.

It was patented in 1986 by Boehringer Mannheim and approved for medical use in 1996.[2]

Medical uses

Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women.[3] In May 2003, the U.S. Food and Drug Administration (FDA) approved Ibandronate as a daily treatment for post-menopausal osteoporosis. The basis for this approval was a three-year, randomized, double-blind, placebo-controlled trial women with post-menopausal osteoporosis. Every participant also received daily oral doses of calcium and 400IUs [international units] of vitamin D. At the study's conclusion, both doses significantly reduced the occurrence risk of new vertebral fractures by 50–52 percent when compared to the effects of the placebo drug.

Ibandronate is efficacious for the prevention of metastasis-related bone fractures in multiple myeloma, breast cancer, and certain other cancers.[4]

Adverse effects

In 2008, the U.S. Food and Drug Administration (FDA) issued a communication warning of the possibility of severe and sometimes incapacitating bone, joint or muscle pain.[5] A study conducted by the American Society of Bone and Mineral Research concluded that long-term use of bisphosphonates, including Boniva, may increase the risk of a rare but serious fracture of the femur. [6] The drug also has been associated with osteonecrosis of the jaw, relatively rare but serious condition.[7]

Pharmacology

Relative potency[8]
Bisphosphonate Relative potency
Etidronate 1
Tiludronate 10
Pamidronate 100
Alendronate 100-500
Ibandronate 500-1000
Risedronate 1000
Zoledronate 5000

Brand names

Ibandronic acid is marketed under the trade names Boniva in the US, Bondronat in Europe, Bonviva in Asia, Bandrone in India, Ibandrix in Ecuador, Adronil in Pakistan, Bondrova in Bangladesh and Bonprove in Egypt, Fosfonat in Mexico.

References

  1. ^ Bauss F, Schimmer RC (March 2006). "Ibandronate: the first once-monthly oral bisphosphonate for treatment of postmenopausal osteoporosis". Therapeutics and Clinical Risk Management. 2 (1): 3–18. PMC 1661644. PMID 18360577.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 523. ISBN 9783527607495.
  3. ^ "Boniva". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  4. ^ Sittig HB (2012). "Pathogenesis and bisphosphonate treatment of skeletal events and bone pain in metastatic cancer: focus on ibandronate". Onkologie. 35 (6): 380–7. doi:10.1159/000338947. PMID 22722461. S2CID 8413102.
  5. ^ "Information for Healthcare Professionals: Bisphosphonates (marketed as Actonel, Actonel+Ca, Aredia, Boniva, Didronel, Fosamax, Fosamax+D, Reclast, Skelid, and Zometa)". U.S. Food and Drug Administration. Retrieved 27 October 2010.
  6. ^ Shane E, Burr D, Ebeling PR, Abrahamsen B, Adler RA, Brown TD, et al. (American Society for Bone and Mineral Research) (November 2010). "Atypical subtrochanteric and diaphyseal femoral fractures: report of a task force of the American Society for Bone and Mineral Research". Journal of Bone and Mineral Research. 25 (11): 2267–2294. doi:10.1002/jbmr.253. PMID 20842676. S2CID 15194275.; Lay summary in: "JBMR Publishes ASBMR Task Force Report on Atypical Femoral Fractures". Journal of Bone and Mineral Research. 14 September 2010. Archived from the original on 9 April 2016. Retrieved 27 October 2010.
  7. ^ "Osteonecrosis of the jaw (ONJ) and drug treatments for osteoporosis" (PDF). United Kingdom: The National Osteoporosis Society. Archived from the original (PDF) on 2017-06-17. Retrieved 2018-08-14.
  8. ^ Tripathi KD (2013-09-30). Essentials of Medical Pharmacology (Seventh ed.). New Delhi: Jaypee Brothers Medical Publisher. ISBN 9789350259375. OCLC 868299888.

External links

  • "Ibandronic acid". Drug Information Portal. U.S. National Library of Medicine.
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